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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1774967Generated: November 2, 2026

Sodium Carbonate → HCID 178434365, compound

https://huagongshe.com/reaction/1774967

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant3-Fluorophenylboronic acidHCID 2733986—
ReactantHCID 178434364HCID 178434364—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 178434365HCID 17843436534.8%

Reaction Conditions

Temperature130 °C

Reaction Steps

Under nitrogen protection, to 6 mL of dioxane was added 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine from Example 102 (0.21 g, 1 mmol), 3-fluorophenylboronic acid (0.28 g, 2 mmol), PdCl2(dppf) (87 mg, 0.1 mmol) and 2 M Na2CO3 (2 mmol, 1 mL). The suspension was heated under microwave radiation at 130° C. for 1 hour. It was cooled to room temperature and the solvent was removed the solvent. The crude product was purified by SGC (EtOAc/Petroleum:1/1) to afford 79 mg (34%) of 122 as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.12 (s, 1H), 7.98 (s, 1H), 7.75-7.82 (m, 2H), 7.44-7.47 (m, 1H), 7.08-7.09 (m, 1H), 2.67 (s, 3H). ESI MS m/z=229 (M+1)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09260425B2
Source datasetuspto-grants-2016_02
ORD IDord-6c72994cc3414574ad8be648aee04f8d
Source noteuspto-grants-2016_02